Di-tert-butyl dicarbonate → [2-(3,4-Dimethoxy-phenyl)-1-methyl-ethyl]-ethyl amine

Participants

Reaction Steps

To all of 2B from the above reaction mixture was added 30 mL of 50% THF in water. To the reaction mixture 1.1 g of sodium bicarbonate was added as a solid followed by 1.35 g (6.18 mmol) of di-t-butyl dicarbonate in 7 mL of THF dropwise over a period of 30 minutes. The reaction mixture was allowed to stir at room temperature for 18 hours, then concentrated under reduced pressure. This was diluted with 50 mL of water and the pH of the solution was adjusted to 5. The aqueous layer was extracted with 3×100 mL of ethyl acetate. The organic layers were combined, dried (anhydrous Na2SO4) and concentrated to dryness. The residue was purified by silica gel column chromatography using 30% ethyl acetate in hexane to give 764 mg (2.58 mmol, 53% from 2A) of 2C as a clear gum (M+Na, 318).

Provenance & Evidence